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CAS No. : | 590422-12-1 | MDL No. : | MFCD11845131 |
Formula : | C7H4FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DLNMLICVXVLIKO-UHFFFAOYSA-N |
M.W : | 153.11 | Pubchem ID : | 45090556 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.79 |
TPSA : | 46.0 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.35 cm/s |
Log Po/w (iLOGP) : | 1.43 |
Log Po/w (XLOGP3) : | 1.24 |
Log Po/w (WLOGP) : | 1.68 |
Log Po/w (MLOGP) : | 1.27 |
Log Po/w (SILICOS-IT) : | 2.46 |
Consensus Log Po/w : | 1.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.18 |
Solubility : | 1.02 mg/ml ; 0.00667 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.8 |
Solubility : | 2.4 mg/ml ; 0.0157 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.08 |
Solubility : | 0.126 mg/ml ; 0.000824 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.38 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In tetrahydrofuran; at 60℃; for 2h; | 1, 1'-Carbonyldiimidazole (11.4 g, 0.0703 mol) is added portionwise to a solution of <strong>[53981-23-0]2-amino-3-fluorophenol</strong> (Step 3, 8. 94 g, 0.0703 mol) in THF (200 ml) and warmed at 60°C for 2 h. The reaction mixture is diluted with ethyl acetate (200 ml), washed with 2N HC1 and saline, dried (MgS04), and evaporated to give product as a white solid suitable for use in the next step (10.6 g, 99percent); mp 131-3°C. |
99% | In tetrahydrofuran; at 60℃; for 2h; | Step 4: Preparation of 4-fluoro-1,3-benzoxazol-2(3H)-one 1,1'-Carbonyldiimidazole (11.4 g, 0.0703 mol) is added portionwise to a solution of <strong>[53981-23-0]2-amino-3-fluorophenol</strong> (Step 3, 8.94 g, 0.0703 mol) in THF (200 ml) and warmed at 60° C. for 2 h.The reaction mixture is diluted with ethyl acetate (200 ml), washed with 2N HCl and saline, dried (MgSO4), and evaporated to give product as a white solid suitable for use in the next step (10.6 g, 99percent); mp 131-3° C. |
59% | In tetrahydrofuran; at 20℃; for 16h; | To a solution of <strong>[53981-23-0]2-amino-3-fluorophenol</strong> (2.5g, 19.6mmol) in THF (5OmL) was added CDI (15.9g, 98.4mmol) at rt. The reaction mixture was stirred at rt for 16h. TLC showed the reaction to be complete. The reaction mixture was diluted with H20 (lOOmL) and extracted with EtOAc (3x lOOmL). The organics were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel (100-200 mesh), eluting with 10percent EtOAc in hexane to afford 4-fluorobenzo[d]oxazol-2(3H)-one as a pale brown solid. Yield:1.8g (59percent); 1H NMR (400 MHz, DMSO-d6): 12.25 (bs, 1H), 7.12-7.19 (m, 1H),7.06-7.12 (m, 2H); MS (ESI-) for CHNOS m/z 151.90 [M-H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid In water at -10℃; for 0.5h; | 86.5 Nitric acid (70%, 2.50 ml, 0.0389 mol) is added dropwise at-10°C to a solution of 4-fluoro-1, 3-benzoxazol-2 (3H) -one (Step 4,5. 95 g, 0.0389 mol) in concentrated sulfuric acid (60 ml). The reaction is stirred at-10°C for 30 minutes and then poured into ice water. The resulting precipitate is collected by filtration and dried under reduced pressure to give desired product contaminated with approximately 10-15% of the undesired 5-nitro isomer (7.2 g, 93%); mp 177-9°C. | |
With sulfuric acid; nitric acid at -10℃; for 1h; | 86.5 Step 5: Preparation of 4-fluoro-6-nitro-1,3-benzoxazol-2(3H)-one Step 5: Preparation of 4-fluoro-6-nitro-1,3-benzoxazol-2(3H)-one nitric acid (70%, 2.50 ml, 0.0389 mol) is added dropwise at -10° C. to a solution of 4-fluoro-1,3-benzoxazol-2(3H)-one (Step 4, 5.95 g, 0.0389 mol) in concentrated sulfuric acid (60 ml).The reaction is stirred at -10° C. for 30 minutes and then poured into ice water.The resulting precipitate is collected by filtration and dried under reduced pressure to give desired product contaminated with approximately 10-15% of the undesired 5-nitro isomer (7.2 g, 93%); mp 177-9° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In N,N-dimethyl-formamide at 60℃; for 2h; | General Procedure II: Synthesis of compounds of Formula II (Scheme 2a) General procedure: General Procedure II: Synthesis of compounds of Formula II (Scheme 2a) l,l'-Carbonyldiimidazole (1.6 eq.) was added to a solution of the optionally substituted aminophenol V (1 eq.) in DMF (2.7 mL per mmol V), and the solution was heated to 60 °C for 2 hours. After cooling to room temperature, the reaction mixture was poured into water (15 mL per mmol V) and extracted with EtOAc (3 χ 15 mL per mmol V). The combined organic phases were washed with brine (15 mL per mmol V), dried over Na2S04, and evaporated on celite. The compound was purified by column chromatography using the Teledyne ISCO apparatus (cyclohexane:EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C 2.1: sodium hydroxide / 2 h / Reflux 3.1: acetyl chloride / ethanol; chloroform / 0.5 h / 0 °C 3.2: 16 h / Reflux 4.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / water; 1,2-dimethoxyethane / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-Bromosuccinimide In acetonitrile at 20℃; for 24h; | |
95% | With N-Bromosuccinimide In acetonitrile at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C 2: sodium hydroxide / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C 2.1: sodium hydroxide / 2 h / Reflux 3.1: acetyl chloride / ethanol; chloroform / 0.5 h / 0 °C 3.2: 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C 2.1: sodium hydroxide / 2 h / Reflux 3.1: acetyl chloride / ethanol; chloroform / 0.5 h / 0 °C 3.2: 16 h / Reflux 4.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 60 °C 2: trifluoroacetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 60 °C 2.1: trifluoroacetic acid / dichloromethane / 20 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.05 h / 20 °C 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.6 g | With potassium carbonate In acetonitrile at 60℃; | 13 Preparation Example 13 To a mixture of 4-fluoro-1,3-benzoxazol-2(3H)-one (27.2 g) and MeCN (500 mL) were added K2CO3 (35.2 g) and bromoacetic acid tert-butyl ester (27.6 mL) at room temperature, followed by stirring overnight at 60°C. The reaction mixture was cooled to room temperature, an insoluble material was separated by filtration, and the filtrate was concentrated under reduced pressure. A mixed solvent of hexane-EtOAc (9:1) was added to the resulting residue and then the obtained solid was collected by filtration, followed by washing with the mixed solvent of hexane-EtOAc (9:1) to obtain (4-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid tert-butyl ester (42.6 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile / 6 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With chlorosulfonic acid at -20 - 70℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C 2.2: 3 h / -78 - -40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C 2.2: 3 h / -78 - -40 °C 3.1: potassium carbonate / 1,4-dioxane; water / 16 h / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C 2.2: 3 h / -78 - -40 °C 3.1: cyanomethylenetributyl-phosphorane / toluene / 6 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C 2.2: 5 h / 0 - 20 °C 3.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C 2.2: 5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C 2.2: 3 h / -78 - -40 °C 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C 2.2: 3 h / -78 - -40 °C 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C 2.2: 5 h / 0 - 20 °C 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C 2.2: 5 h / 0 - 20 °C 3.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: chiralpak IB / ethanol; hexane / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: chlorosulfonic acid / 3.5 h / -20 - 70 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - 20 °C 2.2: 3 h / -78 - -40 °C 3.1: cyanomethylenetributyl-phosphorane / toluene / 6 h / 80 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
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